TAPRENEPAG

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H22N4O5S
Molecular Weight	478.52
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)COC1=CC(CN(CC2=CC=C(C=C2)N3C=CC=N3)S(=O)(=O)C4=CC=CN=C4)=CC=C1

InChI

InChIKey=MFFBXYNKZHTCEY-UHFFFAOYSA-N

InChI=1S/C24H22N4O5S/c29-24(30)18-33-22-5-1-4-20(14-22)17-27(34(31,32)23-6-2-11-25-15-23)16-19-7-9-21(10-8-19)28-13-3-12-26-28/h1-15H,16-18H2,(H,29,30)

HIDE SMILES / InChI

Molecular Formula	C24H22N4O5S
Molecular Weight	478.52
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24720348 | https://www.ncbi.nlm.nih.gov/pubmed/21376717 | https://www.pfizer.com/sites/default/files/product-pipeline/pipeline_2011_0811.pdf

Taprenepag isopropyl (also known as PF-04217329) a prodrug of CP-544326 (active acid metabolite), a potent and selective EP(2) receptor agonist. Taprenepag isopropyl was studied in a clinical trials phase II involving patients with primary open angle glaucoma. According to Pfizer’s pipelines in May 2011, the study was discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin E2 receptor EP2 subtype 5 Target ID: P43116 Gene ID: 5732.0 Gene Symbol: PTGER2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21376717 \| https://www.ncbi.nlm.nih.gov/pubmed/21851167	Agonist 2678		2.8 nM [EC50]

PubMed

Title	Date	PubMed
Effect of PF-04217329 a prodrug of a selective prostaglandin EP(2) agonist on intraocular pressure in preclinical models of glaucoma.	2011 Sep	21376717
A phase 2, randomized, dose-response trial of taprenepag isopropyl (PF-04217329) versus latanoprost 0.005% in open-angle glaucoma and ocular hypertension.	2011 Sep	21851167
Prostaglandin analogues and nitric oxide contribution in the treatment of ocular hypertension and glaucoma.	2019 Apr	29669171

Patents

Sample Use Guides

In Vivo Use Guide

Stage I: 3 cohorts (total n = 67) received 1 drop of taprenepag isopropyl unit dose formulation qPM/eye for 14 days: low dose: 0.0025%, 0.005%, vehicle; middle dose: 0.01%, 0.015%, vehicle; high dose: 0.02%, 0.03%, vehicle. Stage II: 7 groups (total n = 250) received 1 drop of taprenepag isopropyl multidose formulation qPM/eye for 28 days: 0.005%, 0.01%, 0.015% monotherapy; each in unfixed combination with latanoprost 0.005%, or latanoprost monotherapy.

Route of Administration: Other

Substance Class	Chemical Created by `admin` on `Fri Dec 15 19:40:14 UTC 2023` Edited by `admin` on `Fri Dec 15 19:40:14 UTC 2023`
Record UNII	9CD894KUMJ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TAPRENEPAG

Official Name

English

ACETIC ACID, 2-(3-((((4-(1H-PYRAZOL-1-YL)PHENYL)METHYL)(3-PYRIDINYLSULFONYL)AMINO)METHYL)PHENOXY)-

Common Name

English

Taprenepag [WHO-DD]

Common Name

English

PF-04217329

Code

English

PF04217329

Code

English

2-(3-((N-((4-(1H-PYRAZOL-1-YL)PHENYL)METHYL)PYRIDINE-3-SULFONAMIDO)METHYL)PHENOXY)ACETIC ACID

Systematic Name

English

CP544326

Code

English

2-(3-{[{[4-(1H-Pyrazol-1-yl)phenyl]methyl}(pyridin-3-ylsulfonyl)amino]methyl}phenoxy)acetic acid

Systematic Name

English

taprenepag [INN]

Common Name

English

TAPRENEPAG [USAN]

Common Name

English

CP-544326

Code

English

ACETIC ACID, (3-((((4-(1H-PYRAZOL-1-YL)PHENYL)METHYL)(3-PYRIDINYLSULFONYL)AMINO)METHYL)PHENOXY)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568